Gas-liquid flow hydrogenation of nitroarenes: Efficient access to a pharmaceutically relevant pyrrolobenzo[1,4]diazepine scaffold

Dimitriou, E; Jones, R; Pritchard, R; Miller, G; O'Brien, M

doi:10.1016/j.tet.2018.09.025

Gas-liquid flow hydrogenation of nitroarenes: Efficient access to a pharmaceutically relevant pyrrolobenzo[1,4]diazepine scaffold

Dimitriou, E; Jones, R; Pritchard, R; Miller, G; O'Brien, M

Authors

E Dimitriou

Richard Jones r.h.jones@keele.ac.uk

R Pritchard

Gavin Miller g.j.miller@keele.ac.uk

Matthew O'Brien m.obrien@keele.ac.uk

Abstract

Using a Tube-in-Tube device based on the amorphous Teflon AF-2400 fluoropolymer, a series of nitroarenes was hydrogenated to afford the corresponding aniline compounds. The system was then applied to the construction of a pyrrolobenzo[1,4]diazapene scaffold through a tandem hydrogenation-condensation-hydrogenation sequence.

Journal Article Type	Article
Acceptance Date	Sep 11, 2018
Online Publication Date	Sep 18, 2018
Publication Date	Nov 22, 2018
Publicly Available Date	May 26, 2023
Journal	Tetrahedron
Print ISSN	0040-4020
Publisher	Elsevier
Peer Reviewed	Peer Reviewed
Volume	74
Issue	47
Pages	6795-6803
DOI	https://doi.org/10.1016/j.tet.2018.09.025
Keywords	Gas-liquid flow, Hydrogenation, Pyrrolobenzodiazepine, Reduction, Cyclisation
Publisher URL	https://doi.org/10.1016/j.tet.2018.09.025